Observation of Intermediates during the Reaction of Linear Alkanesulfinyl Chlorides with Activated Zerovalent Zinc

Article abstract of DOI:10.1021/jo00177a014

Methane- (2), ethane- (3), propane- (4), butane (5), pentane- (6), hexane- (7), octane- (8), and dodecanesulfinyl chloride (9) reacted with activated zinc to give the corresponding alkanesulfonothioic S-alkyl esters (12-19) in 40-89percent yield.The reaction of methanesulfinyl chloride (2) with activated zerovalent zinc under nitrogen in anhydrous diethyl ether at -30, -20, and 0 deg C was investigated by 1H NMR and 13C NMR spectroscopy.The 13C NMR spectrum of the partially converted -30 deg C reaction mixture showed the presence of methanesulfinyl chloride (2), S-methyl methanesulf onothioate (12), methanesulfinic acid (24) or zinc methanesulfinate (25), methanesulfonyl chloride (26), dimethyl sulfide (27), S-methyl methanesulfinothioate (28), and methanesulfinyl methyl sulfone (29). vic-Dimethyl disulfoxides (31) and OS-methyl methanesulfino(thioperoxoates) (32) are proposed as two of several transient reaction intermediates.